17737 Deer Isle Circle, Winter Garden, FL 34787
For Sale $2,950,000
Save Property
Experience over an acre of elevated direct sunset lakefront luxury living on the naturally spring-fed waters of John’s Lake. Offered publicly for the first time, this fully custom estate represents a rare convergence of beauty, privacy and enduring design. Nearly 5,000 square feet of interior living space unfold effortlessly into an additional 1,000 square feet of exceptionally well-appointed enclosed outdoor living, creating seamless indoor to outdoor living. Positioned within the private gated enclave of Deer Island and presented in impeccable condition since its 2015 construction, the home reflects meticulous care and pride of ownership. Thoughtfully designed for a life well lived by owners and guests alike, every detail was executed with intention. Arrival is elegant and memorable, welcomed by a central fountain and expansive motor court leading to an oversized three-car garage, while two bedrooms on the main level, including the primary and guest suite, provide comfort, privacy and effortless livability for generations. Designed for entertaining, walls of fully retractable sliding glass doors dissolve the boundary between indoors and out, allowing the living and great rooms to open to the terrace beyond. The covered outdoor lounge, finished with a wood-paneled ceiling, gas fireplace and fully equipped outdoor kitchen, extends daily living outdoors. The infinity pool and spa, framed by gas fire bowls, merge seamlessly with the lake view itself, while a dedicated pool access bath enhances convenience. Privately positioned to capture sweeping lake views, the primary suite opens directly to the lanai and features dual walk-in closets. Its bath is anchored by a freestanding copper soaking tub, hammered copper sinks set within custom vanities, and a full stone walk-in shower with multiple showerheads and built-in bench. The kitchen features custom wood cabinetry, oversized island, induction cooktop, separate built-in refrigerator and freezer, professional-grade appliances, and walk in pantry. Architectural details include travertine flooring, coffered and tray ceilings, refined millwork and wrought iron staircase. All closets feature custom built-ins. The second-floor media room may also serve as a spacious fifth bedroom with private balcony overlooking the lake. Beyond the terrace, tiered gardens descend toward the shoreline, where Four Seasons marble statuary is thoughtfully placed throughout the grounds, like a work of art set within the landscape. A private putting green, fire pit and manicured lawn enhance the setting. The composite dock includes dual lifts for boat and jet ski, water and electric service, and upper level sun deck positioned for sunset views. John’s Lake spans over 2,500 acres and is known for exceptional clarity, ideal for skiing, boating, water sports and fishing. Deer Island offers gated entry with waterside tennis, pickleball and basketball courts. The home is serviced by a private well. Less than one mile from the Florida Turnpike and 25 minutes to downtown Orlando. Contact for your private viewing.
Cathedral Ceiling(s)
Ceiling Fans(s)
Coffered Ceiling(s)
Crown Molding
Eat-in Kitchen
High Ceilings
In Wall Pest System
Kitchen/Family Room Combo
Open Floorplan
Primary Bedroom Main Floor
Solid Surface Counters
Split Bedroom
Stone Counters
Thermostat
Tray Ceiling(s)
Walk-In Closet(s)
Window Treatments
Gated
Pickleball Court(s)
Taxes: $24,540.00
Tax Year: 2024
Association Fee: $1,240.00
Association Fee Frequency: Semi-Annually
Condo Fee Frequency: Semi-Annually
Balcony
Fire Pit
Lighting
Outdoor Grill
Outdoor Kitchen
Private Mailbox
Rain Gutters
Sliding Doors
Built-In Oven
Convection Oven
Cooktop
Dishwasher
Disposal
Electric Water Heater
Exhaust Fan
Freezer
Microwave
Refrigerator
Tankless Water Heater
Water Softener
Water
Lake Front
Elementary School: Tildenville Elem
Middle School: Lakeview Middle
Junior High: Lakeview Middle
High School: West Orange High
MLS Area: 34787 - Winter Garden/Oakland
Water: Well
Lot Desc.: Oversized Lot, Sidewalk, Sloped, Paved, Private
Construction: Block, Stucco, Frame
Date Listed: 2026-02-16 18:50:18
Pool: Yes
Pool Type: Chlorine Free, In Ground, Infinity, Lighting, Outside Bath Access, Pool Ala
Private Spa: Yes
Furnished: Unfurnished
Windows: Double Pane Windows, Insulated Windows, Low-Emissivity Windows, Shutters, Thermal Windows, Tinted Windows
Parking: Driveway, Garage Door Opener, Garage Faces Side
Garage Spaces: 3
Flooring: Travertine, Wood
Roof: Tile
Heating: Central, Electric, Zoned
Cooling: Central Air, Zoned
Pets: Yes
Sewer: Aerobic Septic, Septic Tank
Amenities: Gated, Pickleball Court(S)
Listing Courtesy Of: Premier Sothebys Intl. Realty
candace.cassidy@sothebysrealty.com
Experience over an acre of elevated direct sunset lakefront luxury living on the naturally spring-fed waters of John’s Lake. Offered publicly for the first time, this fully custom estate represents a rare convergence of beauty, privacy and enduring design. Nearly 5,000 square feet of interior living space unfold effortlessly into an additional 1,000 square feet of exceptionally well-appointed enclosed outdoor living, creating seamless indoor to outdoor living. Positioned within the private gated enclave of Deer Island and presented in impeccable condition since its 2015 construction, the home reflects meticulous care and pride of ownership. Thoughtfully designed for a life well lived by owners and guests alike, every detail was executed with intention. Arrival is elegant and memorable, welcomed by a central fountain and expansive motor court leading to an oversized three-car garage, while two bedrooms on the main level, including the primary and guest suite, provide comfort, privacy and effortless livability for generations. Designed for entertaining, walls of fully retractable sliding glass doors dissolve the boundary between indoors and out, allowing the living and great rooms to open to the terrace beyond. The covered outdoor lounge, finished with a wood-paneled ceiling, gas fireplace and fully equipped outdoor kitchen, extends daily living outdoors. The infinity pool and spa, framed by gas fire bowls, merge seamlessly with the lake view itself, while a dedicated pool access bath enhances convenience. Privately positioned to capture sweeping lake views, the primary suite opens directly to the lanai and features dual walk-in closets. Its bath is anchored by a freestanding copper soaking tub, hammered copper sinks set within custom vanities, and a full stone walk-in shower with multiple showerheads and built-in bench. The kitchen features custom wood cabinetry, oversized island, induction cooktop, separate built-in refrigerator and freezer, professional-grade appliances, and walk in pantry. Architectural details include travertine flooring, coffered and tray ceilings, refined millwork and wrought iron staircase. All closets feature custom built-ins. The second-floor media room may also serve as a spacious fifth bedroom with private balcony overlooking the lake. Beyond the terrace, tiered gardens descend toward the shoreline, where Four Seasons marble statuary is thoughtfully placed throughout the grounds, like a work of art set within the landscape. A private putting green, fire pit and manicured lawn enhance the setting. The composite dock includes dual lifts for boat and jet ski, water and electric service, and upper level sun deck positioned for sunset views. John’s Lake spans over 2,500 acres and is known for exceptional clarity, ideal for skiing, boating, water sports and fishing. Deer Island offers gated entry with waterside tennis, pickleball and basketball courts. The home is serviced by a private well. Less than one mile from the Florida Turnpike and 25 minutes to downtown Orlando. Contact for your private viewing.
Property Details
Price: $2,950,000
Sq Ft: 4,886
($604 per
sqft)
Bedrooms: 5
Bathrooms: 3
Partial Baths: 2
City: Winter Garden
County: Orange
Type: Single Family Reside
Development: Deer Island
Acres: 1.02
Year Built: 2015
Listing Number: O6381953
Status Code: A-Active
Taxes: $24,540.00
Tax Year: 2024
Garage:
3
Furnishings: Unfurnished
Pets Allowed: Yes
Interior Features:
Cathedral Ceiling(s)
Ceiling Fans(s)
Coffered Ceiling(s)
Crown Molding
Eat-in Kitchen
High Ceilings
In Wall Pest System
Kitchen/Family Room Combo
Open Floorplan
Primary Bedroom Main Floor
Solid Surface Counters
Split Bedroom
Stone Counters
Thermostat
Tray Ceiling(s)
Walk-In Closet(s)
Window Treatments
Amenities:
Gated
Pickleball Court(s)
Financial Information:
Taxes: $24,540.00
Tax Year: 2024
Association Fee: $1,240.00
Association Fee Frequency: Semi-Annually
Condo Fee Frequency: Semi-Annually
Exterior Features:
Balcony
Fire Pit
Lighting
Outdoor Grill
Outdoor Kitchen
Private Mailbox
Rain Gutters
Sliding Doors
Equipment:
Built-In Oven
Convection Oven
Cooktop
Dishwasher
Disposal
Electric Water Heater
Exhaust Fan
Freezer
Microwave
Refrigerator
Tankless Water Heater
Water Softener
View:
Water
Waterfront Description:
Lake Front
School Information:
Elementary School: Tildenville Elem
Middle School: Lakeview Middle
Junior High: Lakeview Middle
High School: West Orange High
Additional Information:
MLS Area: 34787 - Winter Garden/Oakland
Water: Well
Lot Desc.: Oversized Lot, Sidewalk, Sloped, Paved, Private
Construction: Block, Stucco, Frame
Date Listed: 2026-02-16 18:50:18
Pool: Yes
Pool Type: Chlorine Free, In Ground, Infinity, Lighting, Outside Bath Access, Pool Ala
Private Spa: Yes
Furnished: Unfurnished
Windows: Double Pane Windows, Insulated Windows, Low-Emissivity Windows, Shutters, Thermal Windows, Tinted Windows
Parking: Driveway, Garage Door Opener, Garage Faces Side
Garage Spaces: 3
Flooring: Travertine, Wood
Roof: Tile
Heating: Central, Electric, Zoned
Cooling: Central Air, Zoned
Pets: Yes
Sewer: Aerobic Septic, Septic Tank
Amenities: Gated, Pickleball Court(S)
Map of 17737 Deer Isle Circle, Winter Garden, FL 34787
Listing Courtesy Of: Premier Sothebys Intl. Realty
candace.cassidy@sothebysrealty.com